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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 23, Number 9
BKCSDE 23(9)
September 20, 2002 

Correlation of Chemical Shifts with Substituent Parameters in N-Benzyl Derivatives of Pyrrole, 3a,7a-Dihydroindole, and Indole Esters
Kyu Ok Jeon, Ji Sook Yu, Chang Kiu Lee
Single substituent parameter, Dual substituent parameter, Chemical shift, Hyperconjugation
Series of m- and p-substituted benzyl derivatives of pyrrole, tetramethyl 1-benzyl-3a,7a-dihydroindole-2,3,3a,4-tetracarboxylate, and trimethyl 1-benzylindole-2,3,4-tricarboxylate were prepared and their 13C NMR spectra were obtained in 0.1 M solutions of chloroform-d. Both single substituent parameter and dual substituent parameter analyses were carried out to correlate the substituent chemical shifts. The β carbon of the indole series showed the most profound substituent effect dependence as well as the best correlation. The results are explained by the hyperconjugation of the benzyl methylene group.
1241 - 1246
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